Ring Fission of Quinazolines by Means of the Reissert Reaction

スポンサーリンク

概要

• 論文の詳細を見る

• Under the Reissert reaction conditions, quinazoline (1a) afforded 2'-formylbenzanilide (2a), o-aminobenzaldehyde (3a), and N-formylbenzamide (4). Similarly, 4-methyl-(1b) and 4-ethoxyquinazoline (1c) gave the corresponding benzanilides 2b and 2c, respectively, o-aminoacetophenone (3b, from 1b), and benzamide (5). It was confirmed that the same results were obtained in the absence of the cyanide ion. A substituent at the 2-position prevented the ring fission, and only the corresponding N^3-benzoyl pseudo-base (14) was obtained. The generality of the ring fission was shown by the reactions of 1-phenyl-1H-pyrazolo [3,4-d] pyrimidine (6) and 3-phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidine (8), giving 5-amino-1-phenyl-1H-pyrazole-4-carbaldehyde (7) and 5-amino-1-phenyl-1H-1,2,3-triazole-4-carbaldehyde (9), respectively.

• 社団法人日本薬学会の論文
• 1984-09-25

著者

• 五島 綾子

  Shizuoka College Of Pharmacy

• 小久保 宏恭

  Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.

• 林 英作

  Shizuoka College of Pharmacy

• 東野 武郎

  Shizuoka College of Pharmacy

• 林 英作

  School Of Pharmaceutical Sciences University Of Shizuoka

• 小久保 宏恭

  Shizuoka College of Pharmacy

• 竹元 万寿美

  Shizuoka College of Pharmacy

関連論文

• Condensed Pyridazines. VII. : Reaction of 7-(Methylsulfonyl)-1-phenyl-1H-imidazo[4,5-d]pyridazine with Nucleophiles
• Condensed Pyridazines. VI. Reaction of 7-(Methylsulfonyl)-1-phenyl-1H,2,3-triazolo[4,5-d]pyridazine with Carbanions and Enamines(Organic,Chemical)
• Condensed Pyridazines. V. Reactions of 7-(Methylsulfonyl)-1-phenyl-1H-1,2,3-triazolo[4,5-d]pyridazine with Methoxide Ion, Grignard Reagents, Hydrazines, and Amines(Organic,Chemical)
• 縮合環を有するPyridazine誘導体に関する研究(第4報)7-Methoxy-1-phenyl-1H-pyrazolo[3,4-d]pyridazine 5-Oxideの化学的性質
• 縮合環を有するPyridazine誘導体に関する研究(第3報)4,7-Dichloro-1-phenyl-1H-pyrazolo[3,4-d]pyridazineとCarbanion類との反応
• 縮合環を有するPyridazine誘導体に関する研究(第2報)5-Phenylpyrido-[2,3-d]pyridazine 7-Oxideの化学的性質
• 縮合環を有するPyridazine誘導体に関する研究(第1報)5,8-Dichloropyrido-[2,3-d]pyridazineとCarbanionとの反応
• Phthalazine誘導体に関する研究(第14報)Phthalazine2-OxideとAcetylenic Dienophileとの反応
• 環状ヒドラジド構造を含む複素環化合物の合成とその抗腫瘍性について
• Grignard Reactions of 1-Phthalazine-, 2-Ouinoxaline-, and 4-Cinnoline-carbonitrile
• Gel Filtration of Solubilized Systems. V. Effects of Sodium Chloride on Micellar Sodium Lauryl Sulfate Solutions Solubilizing Alkylparabens
• Gel Filtration of Solubilized Systems. I. On the Gel Filtration of Aqueous Sodium Lauryl Sulfate Solution Solubilizing Alkyl Paraben on Sephadex G-50
• Transformation of Quinazoline into 2(1H)-Quinolinones with Alkanoic Anhydrides
• Ring Fission of Quinazolines by Means of the Reissert Reaction
• Gel Filtration of Solubilized Systems. VII. Temperature Effect on the Solubilization of Ethylparaben in Hexaoxyethylene Lauryl Ether Micelles
• Effect of Several Cellulosic Binders on Particle Size Distribution in Fluidized Bed Granulation
• Effect of Several Cellulosic Binders on Particle Size Distribution of Granules Prepared by a High-Speed Mixer
• Quinoxalines. XXII. Aryl Migration of 2-Aroylquinoxalines to 2-Arylquinoxalines
• Studies on Pyrazolo[3,4-d]pyrimidine Derivatives. XIV. : Preparation and Reactions of 1-Phenyl-1H-pyrazolo-[3,4-d]pyrimidine Reissert Compound
• Reactions of the Anion of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) with Electrophiles
• Preparation and Reactions of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile)
• A Novel Skeletal Rearrangement of Aromatic N-Oxides upon Electron Impact
• Quinoxaline 誘導体に関する研究(第24報) : 2-Chloroquinoxaline と各種 C-Nucleophile との反応
• Quinoxaline誘導体に関する研究(第23報) : 2-Chloroquinoxalineと各種Nucleophileとの反応
• Triazolo [4,5-d] pyrimidines. VIII. Aryl Migration of 7-Aroyl-3H-1,2,3-triazolo [4,5-d] pyrimidines to 7-Aryl-3H-1,2,3-triazolo [4,5-d] pyrimidines
• Reaction of 4-Aroylquinazolines with Sodium Hydroxide : Aryl Migration to Give 4-Aryl-3,4-dihydro-4-quinazolinecarboxylic Acids and Formation of Quinazoline and Aroic Acids
• Studies on Pyrazolo [3,4-d] pyrimidine Derivatives. XIII. Aryl Migration of 4-Aroyl-1H-pyrazolo [3,4-d] pyrimidines to 4-Aryl-4,5-dihydro-1H-pyrazolo [3,4-d] pyrimidine-4-carboxylic Acids
• 5-Amino-1-phenyl-1H-1,2,3-triazole-4-carbaoxaldehydeおよび関連化合物のDimroth転位
• Purines. V. Reaction of 9-Phenyl-9H-purine-6-carbonitrile with Nucleophilic Reagents
• Studies on the Reaction of π-Deficient Heterocycles with Aromatic Aldehyde in the Presence of Cyanide Ion
• Studies on the Reaction of Quinazoline with Aromatic Aldehyde in the Presence of Cyanide Ion. I. The Extension of the Benzoin Condensation
• Catalytic Reduction of Heterocyclic Aromatic Amine Oxides with Raney Nickel. II. Reduction of 4-Substituted Quinoline 1-Oxide Derivatives.
• Catalytic Reduction of Heterocyclic Aromatic Amine Oxides with Raney Nickel. I. Reduction of 4-Substituted Pyridine 1-Oxide Derivatives.
• A New Deoxygenation Reaction of an Aromatic Heterocyclic N-Oxides
• Catalytic Reduction of Heterocyclic Aromatic Amine N-Oxides with Raney Nickel. IV.^ Reduction of 4,4'-Azopyridine 1,1'-Dioxide, 4,4'-Azoxypyridine 1,1'-Dioxide, and 2-Styrylpyridine 1-Oxide.
• On the Reaction of Quinazoline with Active Methylene Compound
• Catalytic Reduction of Heterocyclic Aromatic Amine Oxides with Raney Nickel. III. Reduction of Hydroxamic Acid-type N-Oxides.
• On N-Oxidation of 4-Alkyl-, 4-Phenyl-quinazoline and Reaction of 4-Methylquinazoline 1-Oxide
• Triazolo [4,5-d] pyrimidines. V. The Nucleophilic Substitution of 7-Chloro- and 7-(p-Tolylsulfonyl)-3-phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidines
• Triazolo [4,5-d] pyrimidines. VI. 3-Phenyl-3H-1,2,3-triazolo [4,5-d]-pyrimidine-7-carbonitrile and Related Compounds
• Triazolo [4,5-d] pyrimidines. IV. The Grignard Reaction of 3-Substituted 3H-1,2,3-Triazolo [4,5-d] pyrimidines
• Triazolo [4,5-d] pyrimidines. III. The Transformation of 3-Substituted 3H-1,2,3-Triazolo [4,5-d] pyrimidines into 3-Substituted 3H-1,2,3-Triazolo [4,5-b] pyridines
• Triazolo [4,5-d] pyrimidines. II. On 3-Methyl- and 3-Phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidines
• The Transformation of 3,4-Dihydro-4-quinazolinylmethyl Alkyl Ketones into Quinolines
• The Transformation of Pyrido [2,3-d] pyrimidine into 1,8-Naphthyridine
• Mass Spectra of 3-Alkyl-4-cinnolinecarbonitriles
• The Mass Spectra of Pyrido [2,3-d] pyrimidines
• Studies on the Reactions of Pyrido[2,3-d]pyrimidine 3-Oxide with Ketones. The Transformation of Pyrido[2,3-d]pyrimidine 3-Oxide into 1,8-Naphthyridines
• Studies on the Reaction of Quinazoline 3-Oxide with Ketone. The Transformation of Quinazoline 3-Oxide into Quinoline Derivatives
• On the Reaction of 4-Quinazolinecabonitrile with Nucleophilic Reagents. IV. Reaction of 4-Quinazolinecarbonitrile with Active Methylene Compounds.
• On the Reaction of 4-Quinazolinecarbonitrile with Nucleophilic Reagents. III. Reaction of 4-Quinazolinecarbonitrile with Ketones.
• On the Reaction of 4-Quinazolinecarbonitrile with Nucleophilic Reagents. II. Reaction of 4-Quinazolinecarbonitrile with Grignard Reagents.
• Studies on Quinazoline 3-Oxide.
• Phthalazine誘導体に関する研究(第1報) : 1-PhenylphthalazineのN-Oxidationおよび1-Phenylphthalazine 3-Oxideの化学的性質について
• Studies on 4-Chloropyrido [2,3-d] pyrimidine and Pyrido [2,3-d] pyrimidine
• On the Reaction of 1-Chloroisoquinoline and 4-Chloroquinazoline with Several Ketone Carbanions
• Studies on Pyrazolo [3,4-d] pyrimidine Derivatives. V. On the Transformation of 1H-Pyrazolo [3,4-d] pyrimidines into 1H-Pyrazolo [3,4-b] pyridines
• Studies on Pyrazolo [3,4-d] pyrimidine Derivatives. IV. On 1-Methyl-and 1-Phenyl-1H-pyrazolo [3,4-d] pyrimidine 5-Oxide

もっと見る 閉じる

スポンサーリンク